Trimethyltin chloride → HCID 59305031、化合物

HRID 2240250ノート

反応式

HRID 2240250 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:9]=[C:10](I)[C:3]=12.C([Li])(C)(C)C.[CH3:27][Sn:28](Cl)([CH3:30])[CH3:29].[F-].[K+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:9]=[C:10]([Sn:28]([CH3:30])([CH3:29])[CH3:27])[C:3]=12

参加物

6

反応物 4

HCID 14016Trimethyltin chlorideHCID 522689Potassium FluorideHCID 53438252N-Tosyl-4-chloro-3-iodo-7-azaindoleHCID 178418306HCID 178418306、化合物

生成物 1

HCID 59305031HCID 59305031、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

In a Schlenk flask (dried by heating under high vacuum and venting with argon), 1.0 g of 4-chloro-3-iodo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine (2.31 mmol) is initially charged in anhydrous THF (30 ml) and cooled to −78° C. 2.85 ml of tert-butyllithium (1.7 M in pentane) (4.85 mmol) is then slowly added dropwise, and the mixture is stirred at −78° C. for 30 min. 2.42 ml of a 1 M solution of trimethyltin chloride in THF are then added dropwise, and the mixture is allowed to warm to RT overnight. 10 ml of a saturated potassium fluoride solution are then added, and the organic phase is separated off and extracted once with ethyl acetate. The combined organic phases are dried over magnesium sulfate, and the solution is concentrated. The product is purified by column chromatography on silica gel (mobile phase: toluene/ethyl acetate 20:1).

後処理

  1. temperatureto warm to RT overnight
  2. customthe organic phase is separated off
  3. extractionextracted once with ethyl acetate
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. concentrationthe solution is concentrated
  6. customThe product is purified by column chromatography on silica gel (mobile phase: toluene/ethyl acetate 20:1)

出典と根拠

ORDレコード
ord-dce448d63f2b4082b095192af23a8491
出典データセット
uspto-grants-2010_05
特許番号
US07723347B2

反応ノート

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